1.0 2011-09-21 00:20:23 UTC 2015-07-21 06:57:23 UTC FDB022839 N-Oleoylethanolamine N-Oleoylethanolamine (NOE or OEA) is a N-acylethanolamine. N-acylethanolamines (NAEs) constitute a class of lipid compounds naturally present in both animal and plant membranes as constituents of the membrane-bound phospholipid, N-acylphosphatidylethanolamine (NAPE). NAPE is composed of a third fatty acid moiety linked to the amino head group of the commonly occurring membrane phospholipid, phosphatidylethanolamine. NAEs are released from NAPE by phospholipase D-type hydrolases in response to a variety of stimuli. Transient NAE release and accumulation has been attributed a variety of biological activities, including neurotransmission, membrane protection, and immunomodulation in animals. N-oleoylethanolamine is an inhibitor of the sphingolipid signaling pathway, via specific ceramidase inhibition (ceramidase converts ceramide to sphingosine). N-oleoylethanolamine blocks the effects of TNF- and arachidonic acid on intracellular Ca concentration. (PMID: 12692337, 12056855, 12560208, 11997249). N-oleoyl ethanolamine is related to the endocannabinoid anandamide. Endocannabinoids signal through cannabinoid receptors (also stimulated by the active ingredient of cannabis) but although related in structure, synthesis and degradation to anandamide, NOE cannot be considered an endocannabinoid as it does not activate the cannabinoid receptors. Most of the reported responses to NOE can be attributed to activation of peroxisome proliferator-activated receptor-alpha (PPAR-alpha). Administration of NOE inhibits body weight gain in rats. In adipocytes and hepatocytes, NOE inhibits mitogenic and metabolic signaling by the insulin receptor and produces glucose intolerance. It also inhibits gastric emptying, which might act together with the sensory neuronal signals to achieve satiety. NOE is permanently elevated in diabetic obese patients. NOE also reduces visceral and inflammatory responses through a PPAR-alpha-activation independent mechanism (PMID: 17449181). NOE has been shown to be an antagonist of TRVP1 (the transient receptor potential vanilloid type 1 receptor). Overall, NOE has beneficial effects on health by inducing food intake control, lipid beta-oxidation, body weight loss and analgesic effects (PMID: 18704536). [HMDB] N-(2-Hydroxyethyl)-9-octadecenamide N-(2-Hydroxyethyl)oleamide N-(9Z-Octadecenoyl) ethanolamine N-(9Z-Octadecenoyl)-ethanolamine N-(cis-9-Octadecenoyl) ethanolamine N-(Hydroxyethyl)oleamide N-Oleoyl ethanolamine N-oleoyl ethanolamine, Oleoyl monoethanolamide, Oleoylethanolamide N-Oleoyl-2-aminoethanol NOE OEA Oleamide MEA Oleic acid ethanolamide Oleic acid monoethanolamide Oleoyl 1-ethanolamide Oleoyl monoethanolamide Oleoylethanolamide C20H39NO2 325.5292 325.298079497 N-(2-hydroxyethyl)octadec-9-enimidic acid N-(2-hydroxyethyl)octadec-9-enimidic acid 111-58-0 CCCCCCCCC=CCCCCCCCC(=O)NCCO InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23) BOWVQLFMWHZBEF-UHFFFAOYSA-N belongs to the class of organic compounds known as n-acylethanolamines. N-acylethanolamines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine. N-acylethanolamines Organic compounds Organic nitrogen compounds Organonitrogen compounds Amines Aliphatic acyclic compounds Carbonyl compounds Hydrocarbon derivatives N-acyl amines Organic oxides Organopnictogen compounds Primary alcohols Secondary carboxylic acid amides Alcohol Aliphatic acyclic compound Carbonyl group Carboxamide group Carboxylic acid derivative Fatty acyl Fatty amide Hydrocarbon derivative N-acyl-amine N-acylethanolamine Organic oxide Organic oxygen compound Organooxygen compound Organopnictogen compound Primary alcohol Secondary carboxylic acid amide Solid logp 7.02 ALOGPS logs -6.05 ALOGPS solubility 2.91e-04 g/l ALOGPS logp 6.33 ChemAxon pka_strongest_acidic 6.49 ChemAxon pka_strongest_basic 4.46 ChemAxon iupac N-(2-hydroxyethyl)octadec-9-enimidic acid ChemAxon average_mass 325.5292 ChemAxon mono_mass 325.298079497 ChemAxon smiles CCCCCCCCC=CCCCCCCCC(=O)NCCO ChemAxon formula C20H39NO2 ChemAxon inchi InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23) ChemAxon inchikey BOWVQLFMWHZBEF-UHFFFAOYSA-N ChemAxon polar_surface_area 52.82 ChemAxon refractivity 100.94 ChemAxon polarizability 43.06 ChemAxon rotatable_bond_count 17 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 112984 Specdb::CMs 126605 Specdb::CMs 833119 Specdb::CMs 833120 Specdb::CMs 833121 Specdb::CMs 833122 Specdb::CMs 833123 Specdb::CMs 833124 Specdb::MsMs 3411689 Specdb::MsMs 3411690 Specdb::MsMs 3411691 Specdb::MsMs 3411692 Specdb::MsMs 3411693 Specdb::MsMs 3411694 HMDB02088 #<Reference:0x000055ce3258f128> #<Reference:0x000055ce3258ef70> #<Reference:0x000055ce3258edb8> #<Reference:0x000055ce3258ec00> #<Reference:0x000055ce3258ea48> #<Reference:0x000055ce3258e890> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Neutral ceramidase Q9NR71 ASAH2